Production of alkyl sulphates of high molecular weight



Patented Jan. 14, 1936 PATENT OFFICE PRODUCTION OF ALKYL SULPHATES OF HIGH MOLECULAR WEIGHT Heinrich Bertsch, Chemnitz, Germany, assignor to the firm H. Th. Biihme, Aktiengesellschaft,

Chemnitz, Germany No Drawing. Application November 3, 1930, Serial No. 493,243. In-Germany November 4,

13 Claims.

The sulphuric esters of fatty acids obtained by treating unsaturated fatty acids of higher molecular weight, for instance oleic acid or linoleic acid, with concentrated sulphuric acid, have good emulsifying and wetting properties, on account of which they are used as emulsifying, wetting, foaming, and impregnating agents and the like. The principal object of the present invention is to provide a class of preparations of the same i type, but with superior properties. According to the invention such preparations can be obtained by sulphating unsaturated aliphatic hydrocarbons under mild conditions. Especially from unsaturated hydrocarbons with one or several double linkages and containing from to 18 carbon atoms in the chain sulphuric esters of the corresponding hydroxy compounds are obtained, which have high wetting, foaming, and emulsifying properties, and are also very stable towards con- :o centrated acid, alkali, and salt solutions andthe substances causing hardness of water.

The process is preferably performed by treating the unsaturated-hydrocarbon at a temperature of between minus 10 and 0 and while 2:; stirring vigorously with one and a half or two parts of concentrated sulphuric acid.. When treating the higher molecular 'olefines and/or working at very low temperatures it is' preferable to add a thinning medium and solvent, for into stance trichlorethylene, benzene or butyl alcohol, whereby uniform action of 'the sulphuric acid on the whole reaction mass is ensured.

Example 1 obtained for instance by the distillation of spermaceti at reduced pressure, are mixed with kg.

of butyl alcohol and cooled to minus 5 C. The

with 150 kg. of'concentrated sulphuric acid, the

temperature of minus 5 being maintained during the reaction. The following reaction occurs:

100 kg. of cetene' (hexadecylene), which may be mixture is sulphated slowly and while stirring.

Example 2 trated sulphuric acid are added slowly and while stirring the temperature of minus 10 C. being 1 maintained. When the whole qua'ntity of the sulphuric acid is introduced, the excessive sulphuric acid is removed by washing with saturated Glaubers salt solution. The acid washing liquor is separated and the product is neutralized by sodium hydroxide solution. The resulting oily product forms a clear solution with water.

Instead of the initial products mentioned in the examples it is also possible to'use mixtures of unsaturated hydrocarbons of suitable molecular. 9 weight, which can be obtained by the distillation of cracked mineral oils or taroils.

The products obtained by sulphating of olefines, which show the constitution of sulphuric esters of hydroxy compounds corresponding to the ole- L fines used, have very good wetting, emulsifying, and foaming properties and especially the property of imparting a soft, smooth, but not sticky, feel to textile fibers and similar materials. They are thereforesuitable to be added to'treatment liquids of all kinds for use in the textile and leather industries and are also qualified for the use in other technical domains for the purpose of wetting, foaming, dispersing of reagents or of impurities of the treated materials, cleaning, smoothing, and softening. The products are very pure and but slightly colored. They are therefore suitable also for the treatment of materials sensitive to coloring and for the dyeing of light shades. 40

I claim:

1. The production of wetting, dispersing, foaming, and smoothing agents for use in the textile, leather, and other industries consisting in the conversion of unsaturated aliphatic hydrocarbons with not less than 10 carbon atoms into sulphuric estersof the corresponding hydroxy compounds by treating said unsaturated hydrocarbons with mildly acting sulphating means at a temperature not exceeding 0 C. o

2. The production of wetting, dispersing, foaming, and smoothing agents for use in the textile, leather, and other industries, consisting in the conversion of unsaturated aliphatic hydrocarbons with not less than l0carbon atoms into sulphuric 10 droxy compounds by treating said unsaturated taming not less than 10 carbon atoms, by the 10 hydrocarbons with concentrated sulphuric acid at action of a mildly acting sulphating medium at temperatures below 0 C. in the presence of a 501- a temperature not exceeding 0 C. vent and thinning medium, 8. As anew compound, the sulphate ester of 4. The production of agents of the kind set an a iphatic hydroca b av not less h 15 forth consisting in the conversion of unsat- 0 r n m th sulphate radi l b in 15 urated aliphatic hydrocarbons with 19-18 carjoined at a secondary carbon atom. bon atoms into sulphuric esters or the corre- S new Compound, the alkali metal Salt spending hydroxy compounds by treating said of a sulphate ester of an aliphatic hydrocarbon unsaturated hydrocarbons with concentrated having not less t 10 Carbon atoms, the $111- 20 sulphuric acid at temperatures below 0 C. in the phate radical being joined at a S n y a b 20 presence of a solvent and thinning medium and atom. neutralizing the product by addition of alkali 10. As a new compou the Sulphate ester of hydroxide cetene, the sulphate radical being joined at a 5. The production of the sodium compound of secondary carbon atom.

25 the sulphuric ester of cetyl alcohol for use as an 11. As a new compou the Sulphate ester 0f 2,, agent of the kind set forth, consisting in treat decane, the sulphate radical being joined at a ing cetene with concentrated sulphuric acid at secondary carbon atom.

a temperature between minus 10 and 0 in the 12. As a new compound, the sodium salt of presence of butyl alcohol and washing and neuthe sulphate ester of cetene, the sulphate radical 0 tralizing the product. being joined at a secondary carbon atom. w

3. The production of agents of the kind set forth consisting in the conversion of unsaturated aliphatic hydrocarbons with 10-18 carbon atoms into sulphuric esters of the corresponding hy- 6. A wetting, dispersing, foaming, and smoothing composition for use in the textile, leather and other industries, comprising essentially a sulphuric ester derived from an unsaturated aliphatic hydrocarbon containing not less than 10 carbon atoms, by the action of a mildly acting sulphating medium at a temperature not exceeding 0 C.

7. A wetting, dispersing, foaming, and smoothing composition for use in the textile, leather and other industries comprising essentially an alkali metal compound of a sulphuric ester derived from an unsaturated aliphatic hydrocarbon con- 13. As a new compound, the sodium salt of the sulphate ester of decane, the sulphate radical being joined at a secondary carbon atom.

HEINRICH BERTSCH.

CERTIFICATE or CORRECTION.

Patent No. 2,027,896.

January 14, 1936.

HEINRECH BERTSCH.

It is hereby certified that the above numbered patent was erroneously issued to "the firm H. Th. Bohme, Aktiengesellschaft, of Chemnitz, Germany", as assignee oi the entire interest in said invention, whereas said patent should have been issued to American Hyalsol Corporation, of Wilmington, Delaware, a corporat on of Delaware, as assignee by mesne assignments of the entire interest in said invention; page 2, second column, lines 23 and 29, claims 10 and 12 respect 3, for "cetene" read cetane; and that the said Letters Patent should be read with these corrections therein that the same may conform 'to the record of the case in the Patent Office.

Signed and sealed this. 3rd day of March, A. D. 1936.

Leslie Frazer (Seal) Acting Commissioner of Patents. 

